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Anal Sex

Techniques and Positions

 

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Anal penetration of the man by a woman wearing a dildo (pegging)

Pegging is anal penetration of a woman by a woman wearing a strap-on dildo. The origin of the term was a 2001 contest in Dan Savage's Sex advice column, which readers to name the process of a heterosexual woman penetrating her boyfriend with a dildo.


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Enjoyment

The act is (or may be) enjoyable for both man and woman: men get pleasure from stimulation of the anus, rectum, and prostate so long as enough lubricant is applied, and women get stimulation from the base of the dildo against their clitoris or from vaginal penetration if the dildo is double ended. Or a woman can use a vibrator to get pleasure as she fucks her man up his anus.

There is also satisfaction to be had from the reversal of sex roles, particularly the dominance and submission play that can occur during this form of sexual expression. And at least there isn't any danger of an early ejaculation!

Since there is a stigma attached to anal sex (and male homosexuality), it may be that people get enjoyment from gender-reversal aspects of anal penetration with a dildo. And many women enjoy the sense of owning a "penis," while men may being receptive to penetration. 

Popularity of anal penetration

Anal penetration with a dildo has featured in mainstream and pornographic movies; for example, in the 1970 film Myra Breckinridge, although the first explicit scene occurred in The Opening of Misty Beethoven (1976). The documentary Bend Over Boyfriend, produced by Carol Queen, also features it.

Female-to-male strap-ons have a high market value in the porn industry, so a number of studios focus on this subject; the notable ones include Strap It On (black women on white men), a series called Babes Balling Boys, and Strap-on Chicks. There are hundreds of films including this practice, and well-known female porn stars feature strap-on pegging with male partners, among them Taylor Wane and Monique Covťt, who explained: "If women have to take it from behind, then why shouldn't men?"

Strap anal sex on FAQ

Isn't this just weird? And who does this stuff anyway?

Itís becoming more common. Itís not unusual for men to fantasize that a woman is anally penetrating them: some act out their desires. Anal pleasure can be considerable for both sexes, and many men like their female partners to take control in bed.

If a man likes being fucked in the ass, isn't he gay?

No! Being gay is about being attracted to men, not having a predilection for ass-fucking! If a woman does it to a man, it's heterosexual sex. But if he fantasizes about a guy fucking him, as his girlfriend shags him,  he's probably bisexual.

What does it mean when a man enjoys being dominated by a woman?

It means some couples reverse roles as a way of getting more sexual pleasure.

Whatís the best sized dildo for a woman to use on a man?

Start with a small one! To be comfortable, try something 6 inches or less, and move on from there. You need something that fits a harness, so it will have to have a base plate, a sturdy harness, one that has adjustable straps, made of plastic or some other material capable of withstanding the action!

Whatís the best sex position for a woman to fuck a man?

The best position for anal sex is to have the receiving partner lie down on his back, legs pulled up, with his female partner fucking him in a missionary-style man on top position. However, many couples like sex with the man bent over or leaning forward doggy-style - this adds to his submission.

Isnít this really kinky?

It's true many heterosexual couples donít use a strap-on, but if a man enjoys being fucked in the ass by his partner, so what?

Where is the prostate gland and how do you stimulate it?

The prostate gland is situated between the outer wall of the rectum and the point where the penis emerges from the body: it's the size of a walnut and is very sexually sensitive, so that under stimulation it will intensify a manís orgasm and/or the power and quantity of his semen ejaculation.

You can stimulate the prostate with a finger or sex toy inserted through the anus, or you can use a dildo and a suitable butt plug, pushing them about 3 inches into the manís rectum.  Changing the angle of penetration changes the amount of sensation the man gets from prostate stimulation. Press against the wall of the rectum.

Whatís the best artificial lube to use with a strap-on for anal sex?

Water-based lubes are best since they suit all sex toy materials (silicone lubes affect sex toys made of silicone, while oil based lubes affect rubber); good anal lubes are formulated just for anal penetration, and they are heavier, don't lose their slipperiness, and withstand heavy friction.

If the man (or indeed the woman in normal anal sex) is concerned about suffering pain or discomfort, the EROS Explorer anal muscle relaxant spray will protect and relax the area. It allows easy penetration and produces a relaxed opportunity for enjoyable anal sex. There is no loss of sensation, the sensitivity of the anal sphincter is reduced and if your partner is relaxed there will be no discomfort.

Whereís the best place to get a strap-on? 

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How is a single man to find a partner willing to service him in this way?

Paying for sex with a professional dominatrix is a possibility. But many women are more willing to explore the ins and outs of anal penetration than you might think. Indeed, many women will be thrilled to take the chance to reverse roles during sex.

Choosing the Strap-On For You

You need the right equipment for good anal sex - especially when the man is the one who wants to experiment. As mentioned, choose a strong strap-on dildo and add a good quality harness: inexpensive flesh-colored dildos made of rubber with poor quality thin elastic will not last; and it matters what you look like, for an ugly and tastelessly designed strap-on may make you feel cheap.

Harnesses come in corset style and this is both sexy and serviceable; for a more dominant look, choose something that gives you an air of dominance - studded leather, for example.

Donít get hung up on size!

You can't expect to stuff a large dildo up a beginner's asshole: that may well be the end of the experiment. To start with, choose something small and short - you can always get a bigger one later.

As a guide, 5 to 6 inches in length and between 1 and 1.5 inches across is probably about right to start with. use plenty of lube, and choose something firm but flexible; silicone, jelly, and something called Cyberskin are very comfortable. A smooth dildo is best to start with since the anal canal is so sensitive.

And, incidentally, the dildo should be curved for his pleasure: an upward curve will stimulate the prostate and this is likely to give him greater pleasure and more powerful ejaculations. Happily for you both, if it's designed for female G-spot stimulation it can usually be used to stimulate a man's prostate.

Women can become aroused when they use a strap-on. But you can also get physical pleasure by using a vibrator in the harness and one that is designed for stimulating the clitoris or even the vagina as you fuck your man. There are also dual strap-ons, strap-ons designed to penetrate the vagina and anus simultaneously, and so on.....

Wearing Your Strap-On In All Anal sex Positions

You have to get the angle of penetration right or it won't work too well, and the dildo needs to be secured in the right position: the straps should be adjusted so that the dildo hangs at the right angle for all sex positions, though you may need to adjust them as you shift.

Here, the dildo is too low; it should not point downwards, but horizontally out in front or even slightly upwards. If it hangs low, it will be difficult to control.

Here, the straps may cut into your genitals, and the dildo will enter the man at the wrong angle: it needs to be placed over your pubic bone.

Here it is in the correct position. The pubic bone is a firm base for thrusting and helps angle the dildo correctly.

 

WHAT TO DO NEXT

Just how do you fuck your boyfriend? Well, stay calm! Be confident, and assertive. Think of how you'd like a man to be if you were making love for the first time. By asking you to fuck him up the ass, the man is making himself very vulnerable to the woman, and since you are both (presumably) trying to have fun, relax.

The power play may be a turn on for you, and you may find you can explore your whole sexual power. This is the kind of thing that breaks sexual boundaries. 

Start with him bent over as though you were having rear entry sex in the normal way - i.e. as if he was fucking you from behind, but with the positions reversed. Make sure he is the right height.

Find the position that allows for comfortable entry and apply loads of lube to both dildo and his ass-hole. Massage it in with a finger so he relaxes - this is erotic in itself, and if you're into the power play, make him apply the lube to his own ass and to the dildo.

Start gently pushing the tip of the dildo into his anus. Hold the shaft as you do so, and tell him to relax and open up his sphincter muscles until the head of the dildo disappears. when it has gone in a short way, gently let him feel it continue pressing its way in.

Extract from "The Onion"

How do I love my lady's anus? Let me count the ways.......

Have you seen her? Have you seen my beautiful lady and her anus? Unless you are an ex-boyfriend, her proctologist, or an art student in that class she modeled for, you probably have not have glimpsed the fairest orifice on God's green Earth. For this, you have my deepest sympathies.

My lady does not like me to go on and on about her anus, but how can I resist? When I look into that one brown eye, it's like gazing into a deep, untouched lake. Sometimes, it's as if I'm gazing through a taut, puckered window into her very soul, placing myself in danger of being hypnotized by the swirls of her rectum. Her anus is like a vessel I can't seem to fill with enough love, no matter how hard I try. I am not what one would call a holy man, but when I am gently kissing my lady's fragrant anus, I am convinced that there must be a higher power out there who made this sacred aperture.

Itís the (Pelvic) Thrust

Position your hands on his hips and start to push forward slowly until the dildo is right in his butt. Then relax, take a breath and let his asshole and muscles around his anus relax.

Pull a little way out carefully, slowly, and then push back in. Imitate thrusts: Pull out, push in. You wan to carry on with this, gradually increasing your thrusting speed and putting a bit more force in as you go.

Keep thrusting with a steady rhythm. The key thing here is that you're stimulating his prostate gland. This feels good, and you'll find his cock starts dripping pre-cum - he may possibly ejaculate.

Reach around to play with his cock and balls while you enjoy the sense of fucking him from behind. Pay attention to how he reacts: how he moves and the sounds he makes. Judge what to do by the intensity of his moans, what he says, his breathing, and how he moves.

If you fear hurting him, but heís begging you to pound away, trust him. Let yourself go, and remember that communication is important: he must let you know what he wants, especially if he feel any discomfort.

Get Creative!

Once you know what you're doing, experiment with different anal sex positions. Lay him on his back with his legs in the air - you know how it goes, having had sex on your back so many times!

You may want to put his legs over your shoulders, or a pillow under his butt to lift it. Think what he does to you in this position - and then kiss him, play with his nipples or stroke his cock. Or do the reverse woman on top - where he rides your "dick" on top of you!

When the power play really gets going, anal fucking is good for being dominated, so you could try spanking him, or prepare him for anal penetration using a butt plug, or put a cock ring on him to keep him erect and delay his ejaculation. Use all your imagination and think what you have fantasized about doing to men in this position...if you never have, then make it up!

Strap-On Sex Positions 

The best sex positions for strap-on sex with a man. 

Doggy Style 

Get your man face down on a suitable surface - bed, couch, floor, with his head down and his bottom up in the air, supported by pillows under his body if necessary. This is good to start with - he is comfortable and you can see what is happening!

Classic Bend Over Boyfriend 

Another position in which the man is submissive is shown above - he stands, bent over at the waist, supporting his weight with his hands on his knees or on a chair or table. His cock and balls are easily accessible.

Ride 'Em Cowboy

 

This position can work well if he wants to maintain control of the speed and depth of penetration.

 

Extract from Village Voice:  Bend Over, Boys! by Tristan Taormino

Attention all straight men! This is a call to arms. I know the secret to a better sex life. I'm willing to share it with you. There is something you need to learn how to do. Something that can transform your life. You must try it at least once; I am sure you won't be disappointed. You've got something to pick up from your gay brothers. And it's not just those fashion and decorating tips you marvel about on Will and Grace. Something your wives and girlfriends can be taught by their lesbian sisters. No, it's not a crash course in expert muff diving. There is a craze sweeping the nation, and you oughta know about it. It's ass fuckingówith you on the receiving end.

Every single day that I worked at the woman-owned sex-toy store Toys in Babeland, at least one heterosexual couple bought a dildo and harness for her to fuck him. Well, for these adventurous women and their partners, I recommended what I called "My first strap-on"ófor the ride of his (and her) life. It's a slim silicone dildo named Mistress, which I consider to be the best for virgin voyagers, and a simple functional harness. And, of course, I recommended lots and lots of lube.

Other recommended websites on human sexuality:

There are several male sexual dysfunctions which are not much talked about but deserve wider attention - and one of the most important of these is delayed ejaculation. This is a condition during which a man cannot ejaculate during sex of any kind, normal vaginal sex or anal penetrations alike. Admittedly sometimes a man may be able to reach his climax due the tightness of the anus around his penis during thrusting in anal intercourse but it is unusual. For men who need help to deal with the difficulty of delayed ejaculation this is a good resource.


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